Family-friendly holiday rentals in Winter Springs
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winter Springs
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Springs family-friendly rentals
Family-friendly home rentals with a hot tub
Flat in Orlando
4.92 out of 5 average rating, 131 reviewsLuxury & Modern Apartment
18–25 Apr
Guest house in Orlando
4.94 out of 5 average rating, 388 reviewsGarden House near Orlando's cultural hub
5–12 Jun
Apartment in Orlando
4.91 out of 5 average rating, 407 reviewsCozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds
19–26 Oct
Flat in Orlando
4.9 out of 5 average rating, 313 reviewsBeautiful View, Newly Renovated 1 Mile to Disney
21–28 Apr
Apartment in Orlando
4.87 out of 5 average rating, 395 reviewsDELUXE STUDIO NEAR UNIVERSAL/DISNEY/CONVEN. CENTER
29 Oct – 5 Nov
Apartment in Kissimmee
4.84 out of 5 average rating, 250 reviewsLake View Family Condo Disney Universal Orlando
1–8 Oct
Apartment in Orlando
4.97 out of 5 average rating, 297 reviewsLuxurious Waterfront Resort near Disney &Universal
29 Aug – 5 Sep
Townhouse in Kissimmee
4.95 out of 5 average rating, 251 reviewsDisney/Universal Home Away from Home!
14–21 Sep
Family- and pet-friendly home rentals
Guest suite in Orlando
4.78 out of 5 average rating, 525 reviewsPrivate guest suite with enclosed porch
18–25 Jun
Home in Oviedo
4.92 out of 5 average rating, 260 reviews🧡Unique 6/3 ✅Pool ✔Pergola ✅Movie Room ✔UCF, 5⭐s
10–17 Apr
Guest suite in Orlando
4.93 out of 5 average rating, 562 reviewsCharming Comfortable Cottage in College Park
2–9 Aug
Home in Maitland
4.94 out of 5 average rating, 148 reviewsOrlando area pool home in Maitland
4–11 Apr
Home in Sanford
4.95 out of 5 average rating, 157 reviewsHistoric Sanford Sunshine Cottage w/ Treetop suite
19–26 Aug
Tiny home in Orlando
4.82 out of 5 average rating, 499 reviewsThe Ritz- Lakefront Tiny House in Orlando
14–21 Dec
Guest house in Windermere
4.94 out of 5 average rating, 240 reviewsSmall Guesthouse near Orlando's Theme Parks
26 Oct – 2 Nov
Guest house in Orlando
4.96 out of 5 average rating, 367 reviewsThe Coach House- 2 bedroom/3 bath Orlando Getaway!
10–17 Dec
Family-friendly home rentals with a pool
Flat in Sorrento
4.94 out of 5 average rating, 301 reviewsQuiet Neighborhood in the Country
22–29 Jul
Home in Kissimmee
4.84 out of 5 average rating, 205 reviews3 bedroom Villa in Kissimmee
21–28 Apr
Cottage in Kissimmee
4.96 out of 5 average rating, 421 reviewsBright & Cozy Cottage Near Disney
17–24 Sep
Home in Orlando
4.95 out of 5 average rating, 313 reviews*HALF HOME* (read desc) Pool/Disney/Universal
12–19 Jun
Guest suite in Kissimmee
4.86 out of 5 average rating, 567 reviewsPrivate Studio in POOL home
7–14 Jul
Cottage in Kissimmee
4.94 out of 5 average rating, 403 reviewsEntire cottage for 5, close to Disney, Universal!
13–20 Nov
Home in Kissimmee
4.79 out of 5 average rating, 256 reviews3 bedroom Orlando Florida pool home
13–20 Jan
Tiny home in Kissimmee
4.94 out of 5 average rating, 328 reviewsBlue Bungalow Tiny House near all Attractions!!
28 Oct – 4 Nov
Quick stats about holiday rentals that are family-friendly in Winter Springs
Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.6K reviews
Nightly prices starting at
$95 SGD before taxes and fees
Destinations to explore
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Tampa Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- West Palm Beach Holiday rentals
- Boca Raton Holiday rentals
- Naples Holiday rentals
- Fort Lauderdale Holiday rentals
- Miami Beach Holiday rentals
- Miami Holiday rentals
- Key West Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Orlando
- Family-friendly rentals Florida
- Family-friendly rentals Florida
- Family-friendly rentals Kissimmee
- House rentals Winter Springs
- Rentals with a patio Winter Springs
- Pet-friendly rentals Winter Springs
- Rentals with pools Winter Springs
- Monthly Rentals Winter Springs
- Rentals with a washing machine and dryer Winter Springs
- Rentals with outdoor seating Winter Springs
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